Listen to Your Gut

This was inspired by a fan, Pantycladlad. He said he liked cross-dresser stories with some rough treatment. So be warned, there is some non-consent action and a little bit of roughess. Like always, I did it all myself, and although I proofread, there may be a few things I missed. There will be some Midwest regionalisms too. I hope none of it stops you from enjoying the story. This will most likely be a stand alone story unless it is really well received and people want it to continue.

*****

Sometimes, you have to listen to your gut. When it says, "Something bad is about to happen," listen to it and call it a day. I didn't one night and learned my lesson. I should have just called it a night and gone home Saturday.

This is one of those times when I wish I could just tell you a little about me. But telling you only a little about myself won't be enough to prevent a lot of confusion. I am a transgender. I haven't switched completely yet, but soon. I have been on hormone therapy for three full years and living as a woman completely since the year before my freshman year of college. I am completely passable and no one has ever blatantly pointed at me or anything.

I was born 21 years ago as a cute little boy. My parents named me Lyndon, like the former president. They had high hopes I guess. We have had our up and downs, but they still love and support me, even though I have basically managed to crush every one of their dreams. Parents hope for the best for their children and I just never fit into what they wanted for me.

Dad, (Harvey) is big and played football. He hoped I would play and be even better than he was. He wanted a muscular robust boy that would play football and be manly. Well, he got me instead. I topped out at 5'8 and have always been slender and effeminate. I am the opposite of manly. I do like BMX and other bike stuff and can even do a lot of tricks.

Mom, (Nora) wanted a son or daughter that she could dote on and she did. She hoped I would grow up, find a nice spouse, would get married and make her a grandmother. I won't be having any children of my own. Mom gets the daughter but without the benefits of giving birth to my own offspring. Also, since they didn't know how to deal with a transgender child, I was raised as a boy. She didn't even get to do the little dresses and hair and make-up and stuff with me. I wish we had.

They realized how I was early on though. They hoped I would be very smart and the head of my class or something to compensate for my smaller build. I'm average. No honor roll, or anything like that for me. I am a C+ and a B- student. Center of the class, really. In a graduating class of 125 students, I was 61st.

Then we get to top it all off with the bullies. Surprise, surprise, teen-aged boys like picking on the little queer kid. Assholes. I don't even consider myself gay because I always gender identified as a girl. Not that I could explain that to them, I didn't even understand it back then. It's not like they would have cared anyway. I was different and that made me a target. The worst of them was Kyle Brown. He lived three blocks away and he was big and mean; God, why did he have to be so hot?

Yes, sue me, I had a crush on him. No matter how bad he got I couldn't shake my lust for his big tanned body and gorgeous face. We had already graduated and he had plans to go away for college. He made every attempt to ruin my summer before he left. He was a bully, but I don't think he even realized what he was doing to me.

He would dunk me mercilessly at the community pool, but my head would be nestled against his cock while he held me under.

"How do you like that, Linda," he'd yell viciously while laughing with his football cronies."

I could never say, "Oh, I like it just fine!"

He'd steal my bike for a week (the one I built with my graduation money) and ride around the block taunting me with it. He would be in his little summer shorts and shirtless showing how big he was to scare me but all it did was make me drool.

"Wow, this sure is great bike. Bet you wish you were riding, huh, Linda," Kyle called as he rode past for the third time.

I wanted to open my mouth and say, "No the view is much better with you on it." Idiot never even wondered why it fit him perfectly.

He thought he was being mean when he would run past me in the hallway at school those last few weeks and smack my ass, but I about came in my panties every time.

"Have fun trying to sit down, fag," he would sneer as he ran past.

The burning tingle when I sat down made me hard all class. I knew it was wrong but I wanted Kyle even though he was the biggest jerk. This continued until he went off to college.

***********************************

With my parent's consent, I was allowed to begin transitioning before my senior year even let out. My birthday is in November, and we started right after my 18th. During the Christmas break we talked to therapists and specialists and made many of the arrangements. We had taken all the steps with therapists and such and a transition plan was set-up for me. We followed every step to the letter and the week following graduation, Lyndon became Lyndsey. I couldn't become Linda-too many memories.

The whole year was taken up with all the switching needed to be done to change my identity. Wardrobe changes-which I loved! Lifestyle changes-which were tougher than I imagined. My parents were, hesitant doesn't quite describe it, but were determined to make me happy any way that they could. Mom became more and more accepting of the idea and even Dad finally got on board. I lived with them until all my documentation was changed over to Lyndsey. Now, with the slender build and increasingly feminine form and features, I was ready to be Lyndsey full-time. Mom commented on what a lovely girl and made and Dad said he didn't expect it to go so smoothly.

With my hormones and the boob-job I got on my 20th birthday, I looked all-woman. Mom loved the new me. We discussed my surgery and decided to hold off on such a big step so soon. I was going very fast and my therapist suggested slowing down a bit to give things time to sink in. Once the surgery was done, going back would be extremely difficult, if not impossible.

In the fall, I finally enrolled in the community college so I wouldn't have to stay in a dorm. I found small apartment. It was a cute one bedroom place within biking distance from my campus. It was near enough to the State University too and from my small back porch, I could hear the noise on Greek Row whenever they had a party. I even got invited to a few, but I had to work weekend nights.

Mom and Dad were helping with school, but I got a couple part-time jobs to afford living on my own. Since I enjoy working with bicycles, I got a job at a bicycle shop called Wheelies. I worked in assembly and repair, but was starting to do some sales too. I would work there during the afternoon, then ride over to my pizza delivery job. All the riding and not having a bunch of money for junk food had me really in shape. I must have dropped 5 pounds which had me even more slender. My boobs looked a little big on my frame now.

I was getting "checked out" by the cute college guys and some of the customers at the bike shop. I'd get hit on when I delivered pizza too. I dated a couple guys but hadn't gone farther than some heavy making out with them and a little oral action. They always thought that was the foreplay and I had a few close calls with hands up my skirt. I was still too nervous about being discovered.

Thank God for Craigslist and a few not too bad hook-ups. The first guy I met, John was really into me being a t-girl. He was a 35 year old man in town for the weekend only. We met at his hotel and went to dinner together. He constantly remarked how beautiful I looked. His compliments and charm certainly had me feeling good and I blew him in the car on the way back to the room. That was a first for me. I had gone down on the guys I dated but never sucked off a stranger in his car.

In the room, we were in each other's arms before the door shut. We stumbled to the bed and I flipped up my skirt. Carl dragged my panties to the side and licked my puckered little opening. It felt insane. He pulled out a lubed condom and I held my cheeks apart for him. I had been using a ribbed dildo since high school so I knew I was ready for him. He fucked me hot and heavy for the first time in my life. He didn't even realize he had taken my virginity and it felt so much better than my dildo. I came onto the bedspread a couple times that night. I left him my number, but he never called again.

The next guy I met was Bill and he wanted just a casual encounter so we met at a motel. I left information with one of the girls I work with at the pizza place, just in case.

"Go with me when I meet him," I begged Casey.

Casey wrinkled her nose, "That seems weird Lyndsey. All you have to do is ask one of the guys out if you just want a hook-up."

I never told her about me being transgender. I kept begging and I finally wore her down. She dropped me off so she could see him from the parking lot.

To say the sex was good would be an massive understatement. Bill was rough and aggressive. He fucked me every which way he wanted. We did it in the shower, me bouncing on his cock cowgirl style, reverse cowgirl style, doggie, and missionary. We did positions I never heard of and he ruthlessly twisted my smaller form in all kinds of ways. When I stumbled out to my cab the next day I was sore, had some bruises, but was smiling. I did hook up with him a couple more times, usually less furiously, but still fun.

I had a couple not so good times too. Guys who thought they were into it but never wanted to see or touch my penis. They usually had trouble maintaining erections and I left amid apologies and promises to make it up to me. I never contacted any of them again. I longed for the rough treatment Bill had given me and these guys were just too wimpy in the end.

By the time the end of the spring semester starting nearing, I was 21. I was still slender and in shape. My long dark hair had some blue streaks in it and Casey had convinced me on this hot style. My hazel eyes were usually accented with a smoky charcoal eye shadow and my cheeks were smooth and pink. At 5'8, most thought I was a tallish tomboy. My boobs are a modest cup size and I have a golden tan most of the time from visiting the tanning salon twice a week. Hey, a girl deserves to splurge her own money now and then. I got a membership.

I had gotten into the habit of not tucking or even wearing a gaff at all. I was on my bike so often that it just wasn't comfortable. I always dress cute, if a bit tomboyish, but with my height and make-up choices, it works. I wear a pair of capris over-alls and a white t-shirt with the shop's logo on it and my hair in a ponytail when I'm at the bike shop. Whenever I'm selling or working the register, I do tuck and wear tight jeans. I wear a nude color bra under it because a white bra would show through the thin shirt.

I get along great with the guys and the flirting and banter is heavy, but light-hearted. I love my crew. I haven't done anything with any of them except a little making out with the owner Ben. Usually one thing would lead to another when we were there after closing. He even knows about me, but he is married and I won't be a homewrecker. So, I told him I couldn't do that anymore. We still flirt shamelessly but we don't let it get serious. It's fun to have someone who knows but doesn't let that stop us from having some fun.

At my night delivery job, I wear the visor and polo from the pizza place. It's a little hometown place called Mama Mia's. We do some eat-in business, but most of it is carry-out or delivery. Since I'm on my bike so much, I don't tuck and wear a tight pair of panties under some black leggings or spandex biking shorts. My change fanny-pack keeps everything concealed. Plus, show a cute butt and I get some better tips.

This is where Casey works too. We met when I started and we really hit it off. She is my best friend now and we hang out all the time. I plan on telling her about my change soon too. She has no idea even after hanging out all semester. She is a funny blonde, if a bit air-headed. Cliches exist for a reason, people.

That brings us to the Saturday night in question. I had on my polo, visor and leggings. My hair was up in ponytail and sticking out of the visor. I had a hot boy-short and bra combo. The bra made me look even more busty than usual since it lifts my perky boobs perfectly. It was a slow night and my tips were miserable. I got back to Mama Mia's and was cashing out my last run when the phone rang. I was the closest to it so I answered.

"Mama Mia's. This is Lyndsey, will this be dine in or carry-out," I said automatically.

"Uh, hi. This is the Kappa Sigma house. Are you guys still doing delivery? We wanted to place an order," the guy on the phone told me.

I replied, "Oh, sorry, delivery ended at midnight and our last delivery person (me) just cashed out." At least that's what I should have said. Instead, I heard myself saying, "Yea, I suppose we could make one more run for you guys."

I took the order and told him it would be about 20 minutes. I could've sworn I recognized the voice but for the life of me I couldn't place it. This was when my gut started saying this was a bad idea. I ignored it and when their order was ready, I loaded up my bike pedaled over there. I was on my way when I began wondering. Frats are usually 50/50. Either you get stiffed completely, or they are so drunk they go way overboard.

I thought, "Hell, if they stiff me, maybe I'll stay and have a few beers and some pizza before I go. Free food sounded good on my low tips. Plus, I'm done for the night anyway."

I pulled up to the house and the party was in full bloom. It has spilled out into the front yard and circled the house. The music was going loud and I was surprised the cops hadn't arrived yet. Everyone cheered when I arrived with the pizzas. I went up to the door and banged on it. One of the guys out front came over. He was a cute black guy with beer in one of those red solo cups in his hand.

"Hi, you guys ordered some pizza," I yelled over the music.

He opened the door and signaled me in. It was noticeably quieter inside and there were no partiers in here. It was an Inside/Out party. I could see why it was so loud outside, all the speakers had been hauled outdoors so the people outside could hear it.

"Wow, you got here fast." he said, "Can you bring it into the kitchen and I'll get someone to pay you."

I followed in and it was eerily vacant. All the guests were outside. They were dancing in the back yard and the music was blaring out there, but muffled in here. The black guy went to go get someone while I pulled pizza out of the heater bags. I set them on the counter. I opened the fridge and was putting the four 2 liters of Coke in there when someone entered.

"Hey nishe assh, " the voice slurred.

I froze. It couldn't be. Pasting a smile on my face I stood and turned. Kyle fucking Brown. And damn it all, he still looked good.

I replied the only way I could, "Um..thank you."

"Whoa, nice titsh too," Kyle continued.

"Okay. Thanks again," I said trying to be professional, "That's 6 large pizzas and the four liters of Coke. That'll be 88 bucks total."

"Okay, good. Hey, you wanna beer? Go ahead," Kyle suggested. He seemed to be looking at me a little more intently.

Tip or no tip, I decided, the best thing was to leave quickly.

I fibbed and said, "I can't. I would love to, but I have another delivery right after this."

"Do I know you," Kyle asked.

I smiled, "Maybe. I go to school here so you might have seen me around, (this was, of course, a lie.) or maybe you've seen me when I delivered here before." ("I hadn't)

He admitted, "Yea. That could be it."

He reached into his back pocket and pulled out his wallet. He looked real unsteady. He opened the wallet and it was bereft of cash. They were going to try to stiff me on the whole thing. I was sure I was going to have to haul it back.

"Oops. It'ssh up in my room. C'mon," Kyle said and began moving away.

"That's okay. I'll wait here," I told him.

Kyle grinned, "Don't worry, baby. I won't bite. Ha ha. Unless you're into that!"

He wobbled away and I decided to follow. I figured I could get the cash and be out of here that much quicker. It felt like I was heading into a viper's pit though. I was moving farther away from people and was about to be alone with him in his room. Drunken frat guy and lone pizza girl: the whole thing had a serious rapey feel to it.

His room was surprisingly tidy. He stepped in and walked over to his desk where he had a thick stack of money. He put most of it in his wallet, but kept a few bills out.

"Here is the $88 and a $20 for the tip," Kyle said. His slurred speech was gone. The fucker was stone sober. "You could make more if you're willing to have some fun." He flashed me one of those hundreds. "You can have this. The twenty and this making it a total of $120 to you. Just show me those sexy tits of yours."

I hesitated. I was tempted to give him a quick flash for the money. Just then, the door to his room opened up. It was two of his buddies. I thought about trying to run for it, but I wouldn't have gotten past them. They filled the door frame.

"What the fuck, dude," Kyle whined.

The cute black guy from earlier responded, "What's up? We thought you'd be into it by now."

The other guy was cute but in a grungey kind of way. He had that bad boy look about him, an art major I'd bet.

He looked at the other two, "Hey, is this happening or not?"

Kyle sighed, "Waylon, chill. This is happening," he turned to me, "right baby?"

This was spiraling fast. "Run" screamed my gut, but the legs never got the message because I stayed rooted in place. I could not sort out what I should do so I what I always did: I gave in.

I reached down and pulled the shirt up, flashing my bra at the three college boys.

"Uh-uh," Kyle said, shaking his head, "You want the bill, you lift the bra too."

Sighing, I snagged the bra with my fingers and it joined my shirt above my firm perky titties. The three guys cheered and whooped at my display. As horrible as this was, it did feel kind of good to be the center of attention and to have them think I was attractive.

The cute black frat guy moved closer saying, "Damn, those are fine."

"You ain't kiddin', Will," Waylon agreed moving in.

Will reached up and cupped one.

"Hey," I cried pulling my shirt and bra back down.

Will shot Kyle a look, as if imploring him to do something. Kyle pushed the hundred into my hand.

Kyle said, "You can have this fifty too, and everything else so far, if you let us feel them."

If it was anyone else, I could have resisted, probably. This was Kyle Brown though, my nemesis. Even if he didn't know who I was, I was still too scared to say no to him. Too many wet-willies, purple-nurples, noogies, wedgies, and swirlies had taken their toll on my resolve when it came to him. It was easier to just go along with it. I know this is not what we try to believe, but at that moment, I was at his mercy again.

I lifted my shirt and bra again and let the two boys feel me up. Kyle joined in and my eyes closed while I involuntarily moaned. I couldn't help it. The dude gets me so aroused. My tiny cock was leaking pre-cum into my panties and I was so hot.

"Look, man. She's loving it," Waylon pointed out.

My nipples were rock hard and my skin was tingling. The three sets of hands stroked my goose pimpled body and the two guys on either side moved in. They kissed my neck and were sucking on the tender skin and my earlobes. I felt my hands being guided down to bulges. I delicately caressed the packages in my hands through khaki and denim. My head tilted back, eyes closed.